[(3aS,4R,9R,9aR)-4-(1,3-benzodioxol-5-yl)-3a,9a-dihydroxy-5,6,7-trimethoxy-3-oxo-4,9-dihydro-1H-benzo[f][2]benzofuran-9-yl] (E)-2-methylbut-2-enoate

Details

• Internal ID: f8b59373-9932-453b-987a-bd437427c222
• Taxonomy: Lignans, neolignans and related compounds > Lignan lactones
• IUPAC Name: [(3aS,4R,9R,9aR)-4-(1,3-benzodioxol-5-yl)-3a,9a-dihydroxy-5,6,7-trimethoxy-3-oxo-4,9-dihydro-1H-benzo[f][2]benzofuran-9-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2=CC(=C(C(=C2C(C3(C1(COC3=O)O)O)C4=CC5=C(C=C4)OCO5)OC)OC)OC
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@@H]1C2=CC(=C(C(=C2[C@H]([C@@]3([C@]1(COC3=O)O)O)C4=CC5=C(C=C4)OCO5)OC)OC)OC
• InChI: InChI=1S/C27H28O11/c1-6-13(2)24(28)38-23-15-10-18(32-3)21(33-4)22(34-5)19(15)20(27(31)25(29)35-11-26(23,27)30)14-7-8-16-17(9-14)37-12-36-16/h6-10,20,23,30-31H,11-12H2,1-5H3/b13-6+/t20-,23-,26-,27-/m1/s1
• InChI Key: YZRDGLILUWSIQK-UBBUEVTLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₈O₁₁
• Molecular Weight: 528.50 g/mol
• Exact Mass: 528.16316171 g/mol
• Topological Polar Surface Area (TPSA): 139.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.16
• H-Bond Acceptor: 11
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9620	96.20%
Caco-2	-	0.6049	60.49%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6797	67.97%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9017	90.17%
OATP1B3 inhibitior	+	0.9450	94.50%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9760	97.60%
P-glycoprotein inhibitior	+	0.8533	85.33%
P-glycoprotein substrate	-	0.6800	68.00%
CYP3A4 substrate	+	0.6485	64.85%
CYP2C9 substrate	-	0.8043	80.43%
CYP2D6 substrate	-	0.8802	88.02%
CYP3A4 inhibition	+	0.5467	54.67%
CYP2C9 inhibition	-	0.5359	53.59%
CYP2C19 inhibition	-	0.5771	57.71%
CYP2D6 inhibition	-	0.8816	88.16%
CYP1A2 inhibition	-	0.8623	86.23%
CYP2C8 inhibition	+	0.5419	54.19%
CYP inhibitory promiscuity	-	0.6694	66.94%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4254	42.54%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.8920	89.20%
Skin irritation	-	0.7837	78.37%
Skin corrosion	-	0.9370	93.70%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5154	51.54%
Micronuclear	+	0.7833	78.33%
Hepatotoxicity	-	0.5394	53.94%
skin sensitisation	-	0.7638	76.38%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.6307	63.07%
Acute Oral Toxicity (c)	III	0.5042	50.42%
Estrogen receptor binding	+	0.8635	86.35%
Androgen receptor binding	+	0.7550	75.50%
Thyroid receptor binding	+	0.6774	67.74%
Glucocorticoid receptor binding	+	0.8316	83.16%
Aromatase binding	+	0.6008	60.08%
PPAR gamma	+	0.7222	72.22%
Honey bee toxicity	-	0.7178	71.78%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9799	97.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.35%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.08%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.66%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.23%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.72%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.69%	89.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	93.50%	94.80%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	93.06%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.02%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.18%	85.14%
CHEMBL2581	P07339	Cathepsin D	90.68%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.25%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	89.70%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.75%	97.25%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.67%	97.14%
CHEMBL2535	P11166	Glucose transporter	86.17%	98.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.96%	89.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.00%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.60%	99.23%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.42%	93.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	82.14%	82.67%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.76%	96.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.23%	100.00%
CHEMBL2803	P43403	Tyrosine-protein kinase ZAP-70	80.97%	82.50%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.78%	93.40%

Plants that contains it

• Commiphora erlangeriana

Cross-Links

• PubChem: 101201267
• LOTUS: LTS0023291
• wikiData: Q105369413